Low shrinkage dental composite resin containing organic-inorganic functional monomer and preparation method thereof

A technology for low-shrinkage dentistry and dental restoration. It is applied in dental preparations, dentistry, and dental prostheses. It can solve problems such as incomplete solvent removal and material toxicity that does not meet clinical application standards, and achieve excellent comprehensive performance and mechanical properties. Good, reduce shrinkage effect

Active Publication Date: 2016-11-09
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In previous studies, clathrate silsesquioxane was mostly added to the resin matrix in the form of silanized micron silica in the form of solid powder. Since clathrate silsesquioxane is a nanometer-sized material, it is easy to agglomerate. Solvents are often introduced to help disperse during operation, which will cause problems such as incomplete solvent removal and material toxicity that does not meet clinical application standards.

Method used

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  • Low shrinkage dental composite resin containing organic-inorganic functional monomer and preparation method thereof
  • Low shrinkage dental composite resin containing organic-inorganic functional monomer and preparation method thereof
  • Low shrinkage dental composite resin containing organic-inorganic functional monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Preparation of organic-inorganic polyfunctional reactive nano monomer octaepoxy group cage silsesquioxane (Q 8 m 8 E ):

[0038] (1) Add 41.0 mL of tetramethylammonium hydroxide (TMAH), 50.96 mL of methanol, and 15 mL of water into a 500 mL round bottom flask, stir in an ice bath, then add 22 mL of tetraethoxysilane (TEOS), and Stir for 24 hours;

[0039] (2) Add this mixture dropwise to another 1L three-necked flask (500mL n-hexane and 42.9mL dimethylchlorosilane (DMCS) have been added to the bottle, and the mixture is stirred at room temperature for 3h ;

[0040] (3) Separate the liquid with a pear-shaped funnel, take the upper layer liquid and rotary evaporate, filter with suction, wash with methanol for 3 times to obtain a white powder solid, dry to obtain dimethylsilyl clathrate silsesquioxane;

[0041] (4) Add 20 mL of anhydrous toluene and 2.0 g of dimethylsilyl clathrate silsesquioxane into a 100 mL three-neck flask, stir for 5 minutes, add 1.84 mL of al...

Embodiment 2

[0064] 1. Preparation of organic-inorganic polyfunctional reactive nano monomer octaepoxy group cage silsesquioxane (Q 8 m 8 E ):

[0065] Preparation method is with embodiment 1;

[0066] 2. Preparation of spiro ring expansion monomer 3,9-diethyl-3,9 propenyloxymethyl-1,5,7,11-tetraoxaspiro[5,5]undecane (DB-TOSU) :

[0067] Preparation method is with embodiment 1;

[0068] 3. Preparation of silanized micron silica:

[0069] Preparation method is with embodiment 1;

[0070] 4. Mix bisphenol A-glycidyl methacrylate (Bis-GMA) and triethylene glycol dimethacrylate (TEGDMA) evenly in a weight ratio of 7:3 to form a resin matrix for later use;

[0071] 5. Measure 15.2g of resin matrix into a 50mL beaker, add 0.26g of octaepoxy cage silsesquioxane (Q 8 m 8 E ), 0.54g 3,9-diethyl-3,9 propenyloxymethyl-1,5,7,11-tetraoxaspiro[5,5]undecane (DB-TOSU), stir well, ultrasonic 0.5h;

[0072] 6. Add 0.4g camphorquinone (CQ), 0.4g ethyl p-dimethylaminobenzoate (EDAB), 0.4g diphenyl...

Embodiment 3

[0078] 1. Preparation of organic-inorganic polyfunctional reactive nano monomer octaepoxy group cage silsesquioxane (Q 8 m 8 E ):

[0079] Preparation method is with embodiment 1;

[0080] 2. Preparation of spiro ring expansion monomer 3,9-diethyl-3,9 propenyloxymethyl-1,5,7,11-tetraoxaspiro[5,5]undecane (DB-TOSU) :

[0081] Preparation method is with embodiment 1;

[0082] 3. Preparation of silanized micron silica:

[0083] Preparation method is with embodiment 1;

[0084] 4. Mix bisphenol A-glycidyl methacrylate (Bis-GMA) and triethylene glycol dimethacrylate (TEGDMA) evenly in a weight ratio of 7:3 to form a resin matrix for later use;

[0085] 5. Measure 13.6g of resin matrix into a 50mL beaker, add 0.8g of octaepoxy cage silsesquioxane (Q 8 m 8 E ), 1.6g 3,9-diethyl-3,9propenyloxymethyl-1,5,7,11-tetraoxaspiro[5,5]undecane (DB-TOSU), stir well, ultrasonic 0.5h;

[0086] 6. Add 0.4g camphorquinone (CQ), 0.4g ethyl p-dimethylaminobenzoate (EDAB), 0.4g diphenyliod...

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Abstract

The invention discloses a low shrinkage light-cured composite resin for dental restoration and a preparation method thereof. With multifunctional structural advantages, cage-like silsesquioxane can cooperate with an expansion monomer, resin matrix, silanized silica and other components to form a three-dimensional network structure during polymerization so as to reach the purposes of lowering polymerization shrinkage of the material and improving mechanical properties, etc. The preparation method consists of: stirring the components evenly to obtain uncured composite resin, then conducting ultrasonic dispersion, vacuum debubbling, pouring into a mold, visible light curing and other steps, thus obtaining the low shrinkage dental composite resin. The used cage-like silsesquioxane and spiro ortho expansion monomer are both liquid, and have good compatibility with composite resin, and a good dispersion effect can be achieved without introducing a solvent, the added cage-like silsesquioxane provides a network crosslinking point for the system, while the polymerization shrinkage of the composite resin is reduced, the mechanical properties of the material are improved, and the water absorption and solubility are reduced.

Description

technical field [0001] The invention relates to the field of dental restorative materials, in particular to a cage-type silsesquioxane (Q 8 m 8 E ) and spiro ring expansion monomer 3,9-diethyl-3,9 propenyloxymethyl-1,5,7,11-tetraoxaspiro[5,5]undecane (DB-TOSU) A photocurable resin for dental restoration and a preparation method thereof. Background technique [0002] Light-curing composite resins are widely used in the oral cavity because of their good aesthetic properties, bonding properties with teeth, minimally invasive treatment and convenient operability. However, it is also found clinically that volume shrinkage and shrinkage stress during resin polymerization can lead to micro-leakage or ineffective bonding at the resin-tooth interface, which in turn leads to the occurrence of secondary caries. Therefore, how to reduce secondary caries after resin restoration and further improve the mechanical properties of resin has become one of the key issues to be solved in the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K6/083A61K6/027C08F222/20C08F216/12C08F2/50
CPCA61K6/831A61K6/889C08F2/50C08F222/1006C08L35/02C08F222/102C08F216/125
Inventor 李齐方张宏婷陈广新
Owner BEIJING UNIV OF CHEM TECH
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